1,6-Enyne Cyclizations Catalyzed by N-Heterocyclic Carbene Supported Gold Complexes: Deconvoluting Sterics and Electronics

被引：25

作者：

Arumugam, Kuppuswamy ^{[1
,2
]}

Varghese, Bibin ^{[1
]}

Brantley, Johnathan N. ^{[1
]}

Konda, Sai S. M. ^{[1
]}

Lynch, Vincent M. ^{[1
]}

Bielawski, Christopher W. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

[2] St Bonaventure Univ, Dept Chem, St Bonaventure, NY 14778 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 03期

基金：

美国国家科学基金会;

关键词：

N-heterocyclic carbenes; Gold; Isomerization; Enynes; Steric hindrance; INTERMOLECULAR ADDITION; EFFICIENT; PLATINUM; LIGANDS; CYCLOISOMERIZATIONS; HYDROXYCYCLIZATION; ALKOXYCYCLIZATION; HYDROAMINATION; HYDROARYLATION; REARRANGEMENT;

D O I：

10.1002/ejoc.201301137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of N-heterocyclic carbene (NHC) supported gold(I) complexes were synthesized, characterized in solution as well as in the solid state, and examined as precatalysts for 1,6-enyne cycloisomerization reactions. The product mixtures obtained for a variety of 1,6-enyne isomerizations were governed primarily by the electronic properties of the aforementioned precatalysts. In particular, precatalysts containing electronic-rich NHC ligands showed increased selectivity for bicyclic products, whereas analogous precatalysts supported by electron-deficient NHCs preferentially afforded olefinic products.

引用

页码：493 / 497

页数：5

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